Triethylamine → N-[2-(Benzyloxy)benzoyl]-L-serine benzyl ester

HRID 2185972Notes

Reaction equation

HRID 2185972 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:19]([O:26][C:27](=[O:32])[C@H:28]([CH2:30][OH:31])[NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:26][C:27](=[O:32])[C@H:28]([CH2:30][OH:31])[NH:29][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 18105812-Benzyloxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12930233Benzyl L-serinate--hydrogen chloride (1/1)

Product 1

HCID 70173311N-[2-(Benzyloxy)benzoyl]-L-serine benzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(benzyloxy)benzoic acid (2.0 g, 8.7 mmol), L-serine benzyl ester hydrochloride (2.0 g, 8.7 mmol, 1 equiv.) and HOAt (1.2 g, 8.7 mmol, 1 equiv.) in DMF (200 mL) was added triethylamine (0.98 mL, 9.6 mmol, 1.1 equiv.) and EDC HCl (2.02 g, 4.8 mmol, 1.2 equiv.). After being stirred overnight at room temperature under nitrogen, the reaction mixture was diluted with ethyl acetate (200 mL), washed with 1N HCl (60 mL), saturated NaHCO3, saturated NH4Cl (60 mL), and brine (60 mL). The combined organic layers were dried over Na2SO4, filtered, concentrated and chromatographed on silica gel eluting with CH2Cl2/MeOH (95/5) to give the title compound, N-[2-(benzyloxy)benzoyl]-L-serine benzyl ester, 92.5 g, 70%) as white crystals. Rf=0.5 (CH2Cl2/MeOH, 95/5); 1H NMR (300 MHz, CDCl3) δ8.80 (d, 1H, NH), 8.19 (dd,1H, ArH), 7.46-7.24 (m, 11H, ArH), 7.12-7.04 (m, 2H, ArH), 5.21-5.11 (m, 4H, 2{CH2phenyl}), 4.91-4.87 (m, 1H, CH), 3.93-3.90 (m, 2H, CH2OH), 2.2 (1H, OH).

Workup

  1. washwashed with 1N HCl (60 mL), saturated NaHCO3, saturated NH4Cl (60 mL), and brine (60 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel eluting with CH2Cl2/MeOH (95/5)

Sources & evidence

ORD record
ord-212378c3826744abaae803b4315283d4
Source dataset
uspto-grants-2002_06
Patent number
US06403623B1

Reaction notes

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